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This reagent reacts with a ketone or aldehyde in a Wittig reaction to give an enol ether, which can be converted to the aldehyde by acid-induced hydrolysis. The initial report of the reaction demonstrated its use on the steroid tigogenone. It was later used in the Wender Taxol total synthesis and the Stork quinine total synthesis.
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. [1] [2] [3] Most often, the Wittig reaction is used to introduce a methylene group using ...
The alkylphosphonium salt is deprotonated with a strong base such as n-butyllithium: [Ph 3 P + CH 2 R]X − + C 4 H 9 Li → Ph 3 P=CHR + LiX + C 4 H 10. Besides n-butyllithium (n BuLi), other strong bases like sodium and potassium t-butoxide (t BuONa, t BuOK), lithium, sodium and potassium hexamethyldisilazide (LiHMDS, NaHMDS, KHDMS, where HDMS = N(SiMe 3) 2), or sodium hydride (NaH) are also ...
Methylenetriphenylphosphorane is prepared from methyltriphenylphosphonium bromide by its deprotonation using a strong base like butyllithium: [1]. Ph 3 PCH 3 Br + BuLi → Ph 3 PCH 2 + LiBr + BuH
A 1,2-Wittig rearrangement is a categorization of chemical reactions in organic chemistry, and consists of a 1,2-rearrangement of an ether with an alkyllithium compound. [1] The reaction is named for Nobel Prize winning chemist Georg Wittig. [2] [3] The intermediate is an alkoxy lithium salt, and the final product an alcohol.
It undergoes a Wittig reaction. [1] It is used in the Vitamin B12 total synthesis. Production
The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. [1] The Horner–Wadsworth–Emmons reaction. In 1958, Leopold Horner published a modified Wittig reaction using phosphonate-stabilized carbanions.
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5) 3 and often abbreviated to P Ph 3 or Ph 3 P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry.